MicroConf Mastermind Matching Program
Rob Walling had been a vocal advocate for startup masterminds for over a decade, having personally experienced their transformative impact on his entrepreneurial journey. He joined his first mastermind roughly 13 years ago and credits it with being instrumental to his success. When he and the team at MicroConf began receiving frequent questions from founders asking "Where do I find a mastermind?" they realized there was a clear market gap—while masterminds existed, there was no systematic way for founders to be matched with complementary peers.
MicroConf launched their Mastermind Matching Program over the course of three years, developing a matching algorithm based on key data points: ARR, team size, previous entrepreneurial experience, goals, and individual strengths and weaknesses. The program curated groups by revenue level, ensuring that pre-revenue founders received different guidance than those doing millions in ARR. The results were impressive: nearly 1,000 founders were connected around the world, collectively building businesses with over $150 million in combined ARR.
The program's success prompted refinement based on founder feedback. The most common request was for more guidance and mentorship alongside peer support. Rather than just matching founders and letting them figure it out, MicroConf recognized that structured support drove better outcomes. This led to a relaunch with major updates: an all-hands Mastermind 101 orientation meetup, a curated three-month series of conversation starters and action items, and access to two mentor sessions with world-class founders and consultants covering topics like customer interviews, hiring decisions, and marketing flywheels.
The relaunched program now offers tiered benefits based on founder stage and ARR. Founders who have reached $500K+ ARR can attend monthly office hours with Rob Walling and co-founder Ann Arvolset, where they discuss challenges in a small, non-public setting. Rob's experience across 127 investments and multiple companies means he has seen most scenarios founders face, allowing him to provide advice that can save weeks or months of painful learning. The program operates on a sliding scale pricing model, with applications closing on February 3rd at microconf.com/masterminds.
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